Here's the situation: A friend told me that someone had gotten nude pictures of his GF and combined them with a picture of her from her Facebook in which she's dressed in her organization's uniform, and sent it to some other members of the organization. One recipient reported it to the admins and they blocked any more of the emails getting to others. They reported the situation to the police.
However, he asked me to help him figure out how someone could've gotten those pictures. He told me that he and her did things on Skype (while he's away on business, etc), and he'd taken some snapshots, but he swore that he didn't even tell anyone else stuff like that existed. He did check his collection and found the two nudes in it though, they were dated several months apart and a bit different (he showed them to me). The ones used in the picture had different coloration and horizontal lines as you see when you take a picture of a computer screen with a camera. Unfortunately, the picture taken from Facebook was open to the public, so that's a dead end. But we can assume that the person knows of the organization and at least knows of him and his GF as the picture was first sent to people they're close to.
The dude is moderately security conscious, and says all those pictures are only on his laptop which he doesn't lend to anyone and always locks whenever he goes out, even though he mostly keeps it at home. But now he thinks that his entire collection could possibly be out there somewhere and is afraid the person(s) might send more pictures another time. Said his GF is still pretty shocked and depressed about the whole thing. She gave him the email address and possible name of the sender, which she got from one of the persons who received the picture, but that address is probably fake.
Right now the main thing we're trying to figure out is the possible ways those pictures could've gotten out and plug the hole. Is it possible that Skype connections can be hacked? Maybe some kind of malware on his or her computer? Maybe something there from before the first pic was taken till after or later, or something that just chose a couple pictures at once? Could someone have hacked into his computer and taken the pics? Also is there a way to track the email (without going to the authorities or something), which would hopefully lead to the person(s)? How can we go about getting more information about this?